Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Top Pittsfield Hotels with Bars

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (743)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is NT$2,658
NT$2,969 total
includes taxes & fees
Nov 2 - Nov 3
Berkshires Untold
Element Lenox Berkshires
Exterior

Element Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (5)
"New hotel very nice"
The price is NT$4,617
NT$5,157 total
includes taxes & fees
Nov 2 - Nov 3
Element Lenox Berkshires
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (887)
"Excellent customer service and great rooms"
The price is NT$3,129
NT$3,495 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Courtyard by Marriott Lenox Berkshires
Property amenity

Courtyard by Marriott Lenox Berkshires

3.0 star property
9.2 out of 10, Wonderful, (575)
"Fabulous place"
The price is NT$3,979
NT$4,445 total
includes taxes & fees
Nov 2 - Nov 3
Courtyard by Marriott Lenox Berkshires
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (777)
"Great property! Very large clean room in a unique hotel! "
The price is NT$3,827
NT$4,275 total
includes taxes & fees
Nov 3 - Nov 4
Hotel On North
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (647)
"We always stay at the Garden Inn when visiting the Berkshires."
The price is NT$4,054
NT$4,529 total
includes taxes & fees
Nov 2 - Nov 3
Hilton Garden Inn Lenox Pittsfield
Willows Motel Williamstown
Exterior

Willows Motel Williamstown

2.0 star property
9.0 out of 10, Wonderful, (957)
"Very quaint inn, comfortable beds, very clean. Most cheerful staff and great fresh fruit and variety at breakfast."
The price is NT$2,706
NT$3,023 total
includes taxes & fees
Oct 7 - Oct 8
Willows Motel Williamstown
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (745)
"The lodging was convenient to all the area attractions."
The price is NT$3,527
NT$4,363 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Cozy Corner Motel
Exterior

Cozy Corner Motel

2.0 star property
9.2 out of 10, Wonderful, (865)
"Very nice staff, nice breakfast"
The price is NT$2,269
NT$2,678 total
includes taxes & fees
Nov 2 - Nov 3
Cozy Corner Motel
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (60)
"Atmosphere, service and food was excellent. Definitely going back!"
Little Cat Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Pittsfield Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 4 days ago
The Red Lion Inn

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Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 73 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: Enjoy the bar, free WiFi, and free parking.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Barrington Stage Company, and then find a cozy spot for a nightcap. Other places to see include Bousquet Ski Area and Hancock Shaker Village. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.